


Winslow

by BridgetteIrish



Series: Winslow [1]
Category: Supergirl (TV 2015)
Genre: A bit of Supercat, But mostly Cat and Winn being adorable awkward friends, Cat/Winn Brotp, F/F, Friendship
Language: English
Status: Completed
Published: 2017-06-07
Updated: 2017-06-07
Packaged: 2018-11-10 01:22:22
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11116920
Author URL: https://archiveofourown.org/users/BridgetteIrish/pseuds/BridgetteIrish
Summary: Amidst all the turmoil they have been through and witnessed while trying to keep Kara safe and sane, Winn and Cat find in each other an unusual but enduring friendship.  A series of scenes showing the progression of this friendship.





	Winslow

**Author's Note:**

> A big thanks to reginalovesemma for the edits and for buying into this little brotp with me.

He was playing Minecraft and fighting back tears when the heavy-bottomed tumbler thumped on his desktop and the shapely figure of his boss planted itself against the front, next to his chair. It was exactly where Kara had stood, just minutes before, and told him she didn’t want things to change between them. She’d broken his heart with tears in her eyes and while he tried so hard not to be angry, it had proven an impossible feat.

He knew he wasn’t supposed to be mad. He knew he was supposed to be supportive and accept the friendship being offered. He knew, ultimately, her happiness was the most important thing, but the evil thought that kept running through his mind was… what about my happiness?

He followed the line of Cat’s hip where it leaned against his desk and met her eyes before his own could get too caught up lingering in places that could get him fired… or killed. For a split second his fear overwhelmed his sadness and he stuttered. “H-Hi, Miss Grant. Did you need something? Something techy?” He rolled his eyes internally at his idiocy and picked up a Superman stress ball to give his hands something to do.

Cat’s manicured finger tapped the edge of the glass twice. “I often find that a good scotch hurts enough going down that the rest of the pain fades away temporarily.”

Winn’s face fell and he turned back to his game. “I don’t know what you’re talking about.”

“Oh come on, Winslow.” Winn snapped his head up at her use of his full name. “I may not have Kiera’s superhearing, but I know a ‘let him down easy’ conversation from a mile away.” She held up a hand. “Please don’t deny it. She’ll never know I know. Just… drink. And if that one doesn’t dull the pain, come in and have another. Then go home. Tomorrow, after she’s gone, we can do this all over again.”

Winn picked up the glass and swallowed the two fingers of thirty-year-old Macallan in one go. This set off a coughing fit so severe he had tears running down his face. He barely registered Cat patting his back forcefully. “Good boy, Winslow. Call it a night. See you in the morning.”

Winn gathered his things, shut off the tiny lamp at the corner of his desk and turned to give Miss Grant a thank you. What he saw stopped him in his tracks. Cat Grant had poured her own two fingers of scotch. He clutched the strap of his messenger bag and watched as she downed it at once, poured two more and leaned her hands heavily against the bar, letting her head drop forward. She couldn’t see him lingering through the curtain of blonde curls, so he turned quickly on his heels and left before she caught him staring.

The next evening, after a fraught day of avoiding Kara’s eye contact and trying to look busy even though he couldn’t concentrate on anything, he heard Kara attempt a cheery “Bye Winn,” before heading to the elevators. There was no mirth in her voice though. It came out flat and dull and sad and it reminded him that she was probably hurting too. He had tried, no less than half a dozen times that day, to approach her desk and apologize in some grand fashion, but each time his embarrassment and fear and that frustrating anger stopped him. He knew she wasn’t obligated to like him and he was angry that he couldn’t let that be enough.

When the elevator doors closed on Kara, he leaned forward and thumped his head against his keyboard, sending the screens into flashing chaos and causing a high-pitched whine to come from the speakers on his computer.

The thump of the whiskey tumbler made him pop his head up where Cat Grant peered down at him like an avenging angel. “Romantic Entanglement is not a valid reason to destroy company property, Winslow. Now, drink up.”

“I don’t think I should, Miss Grant. I’ll stick to beer. That stuff is…”

“More per glass than your monthly cardigan budget.” She smiled and lifted her own glass to her lips. 

Winn took a pull, careful not to drink the entire glass. He let out one healthy cough and clinked his glass against Cat’s before taking another tiny sip. He indulged himself in a tiny moment of surrealism at drinking bourbon with Cat Grant at work. 

“That’s more like it. You’ll get used to it.” She leaned against his desk just as she had the night before. “Did you talk to her today?”

Winn shook his head. “I wanted to. I’m humiliated.” He sipped again and leaned his elbows on his knees. He pondered for a second on how much to reveal, but there was something about the way Cat could pull the truth from people that made him want to confide in her. He pressed on. “What you don’t know, is that I kissed her. Now every time she looks at me, that’s all she’ll remember. God I’m such an idiot.”

Cat rolled her eyes. “Oh Winslow. Would you really want to start some rushed love affair, only to find out later that the two of you have nothing in common beyond cardigans and capes?”

Winn shrugged. “It might have been nice to try.”

Cat polished off her scotch and sauntered back into her office to refill at the bar, talking to Winn over her shoulder all the way. “Take it from someone who’s been there. There’s more heartache in the ‘try’ than in the ‘what if’.”

The scotch had begun to go to Winn’s head so he didn’t think twice about following Cat toward her office. He leaned against the glass doorjamb and waited for permission to enter. “C’mon, Miss Grant. Who wouldn’t want you?” His eyes went impossibly wide and he drained his glass and held in his cough.

Cat laughed openly. “Nobody, silly boy, well, except Idris Elba, I suppose. His loss.” She crossed to her sofa and sat, gesturing to the seat across from her as an invitation. Winn sat as Cat continued. “My ex-wife was my best friend for years. She was beautiful, charming, brilliant and she adored my son. On paper,” Cat sipped and leaned forward, her focus entirely on the amber liquid in her glass, “she was flawless.” Cat’s fingers were turning the glass in her hand, almost as though she’d forgotten Winn was there.

“But?” Winn was genuinely curious, but the sadness in Cat’s eyes was unfamiliar. Something in him was compelling him to reach out, even if he got his hand bitten in the process. 

“But when she kissed me after years of being friends, I… felt nothing. No spark, no… chemistry.” They both smiled at the joke and sipped in tandem. It was well-known that Cat’s very public last marriage was to a Nobel Prize-winning chemist. “But she was stable and loving and I wanted that for Carter. So, I kept up the relationship… for far longer than either of us deserved…” Winn met her eyes, which were shining with tears. “And now… we can’t even be in the same room together.” Her eyes went steely and she slid forward to lay her hand over Winn’s on his rocks glass. “You don’t want to lose her friendship, Winslow. I promise, the gift she’s offering you is far more precious than the one you’re reaching for.”

Winn sighed. She was right, of course. And it would be up to Winn to reach out. He resolved then and there to do just that. “Thanks, Miss Grant. I can see now why Kara turns to you. It really might be your superpower.”

Cat smiled a bit sadly. “Carter’s home this week. I need to go.”

“Yeah! Oh my god, yeah. Of course. Sorry. Sorry.” He took her glass from her and crossed to set them on the bar. “I’m gone. Thanks for the… gasoline… again.”

“Goodnight, Winslow.”

Winn stopped and found a final bit of courage before he exited the office. “Miss Grant?”

Cat looked up from where she was putting her tablet into her oversized handbag. 

“Why do you call me Winslow?”

“It’s your name, isn’t it?”

Winn shrugged. “Well, yeah, but you never knew it before and you called me Toyman Jr. when my dad…” he trailed off, not quite trusting his voice and absolutely refusing to cry in front of Cat Grant. “You don’t even call Kara by her name. I know you know it.”

Cat slung her bag over her elbow and crossed the room, prepared to leave. “I’ve watched you, these past few days, face down the man who gave you that name, conquer your fear of it. You are not him, Winslow..” She raised her eyebrows at him. “Don’t get used to hearing it in a full bullpen,” she said with a point of her finger.

Winn was still feeling brave. Later, after Cat scratched his eyes out for his impertinence, he would blame the scotch. “What about Kara? Why don’t you call her by her name?”

Cat sighed and leaned against the doorjamb across from Winn, crossing her arms. “Kara… has much to learn about her own legacy. I watched her cousin learn how to do this in Metropolis. She’ll get there. Help her as much as you can.” She gave Winn an affectionate pat on his shoulder and made her way to the elevator, leaving him alone in a stunned silence.

XX

Winn’s heart dropped as Kara left Cat’s office that evening. She didn’t just look on the verge of tears. She looked like her entire world had shattered. He rushed to her desk as she began shoving things in her purse. “Kara, what happened?”

“Nothing, Winn. I’m fine. I’ll see you tomorrow.”

He cut her off on her way to the elevators. “You sure? You don’t look fine. We could do a milkshake and french fries night?”

Kara shook her head and he knew instantly she wasn’t interested in company. “Not tonight, Winn. I’m just gonna patrol for a bit and hit the hay.” She managed a small smile. “I’ll see you tomorrow.”

He stepped aside and watched her until the elevator door closed behind her. He spun around to look into Cat’s office and was met with steely eyes behind distinctive reading glasses that were fixed on a spot over his shoulder. It occurred to him that she, too, had watched Kara walk away and he now recognized that rare pain hiding behind her wall of bravado. His heart gave a compassionate little thump and he was struck with a brilliant, stupid idea.

A couple minutes of rummaging through his desk drawers produced a family size package of Red Vines and his old PS3. He tapped on the glass with a knuckle and took Cat’s annoyed eyeroll as permission to enter her domain.

“I know you use my office as a rec room when I’m away, Winslow. Up until now you’ve at least had the good sense to wait until I’m out of the building first.”

His first instinct was denial. “What? Miss Grant. I don’t… I haven’t… Alright, that happened once, with Carter, but it was a special circumstance.”

Cat removed her glasses and sighed in exasperation. “What do you want, Witt?

The incorrect name almost had him fleeing back to his own desk, but he remembered how comforting it was for someone just to notice when he was hurting, so he dug up his spare courage and strode forward. “I won’t ask what happened with Kara just now, but, I think it may be my turn to help you work through some heartache.”

“Don’t be ridiculous. Kiera and I had a disagreement. She’s lucky I didn’t fire her.” The glasses went back on and Cat turned back to her work. She waved him off. “Run along.”

“I will. I promise, but first…” He crossed to her desk and laid the package of Red Vines next to her arm. He pulled one out and held it in front of her face. “Just have one.” She looked at him with something very much like murder in her eyes, but he found, oddly, that he wasn’t afraid. “You have scotch… I have Red Vines.” Cat took a bite from the candy almost in defiance and peered up at him with that same murderous glare. 

Winn sprung back into action. As he spoke he began setting up the game console to project on the screens behind Cat’s desk. “Now, I also find that killing zombies is also very therapeutic and since zombies are not real… yet… we have,” he held up his favorite stress relief game, “The Walking Dead.” Cat didn’t speak as he ran through the buttons and actions in a brief crash course. When he was finished, he laid the controller next to the Red Vines and stood back, shoving his hands in the back pockets of his pants. “Okay. I’ll go now, Miss Grant. See you tomorrow.” 

Winn left the office and grabbed his bag from his desk. When he was halfway across the bullpen, Cat’s voice finally rang out on the empty floor. “Winslow.” He turned to face her and was struck by the sad smile on her face. “Thank you.”

Winn clutched the strap of his bag and left.

XX

Winn had spent the last few hours of his day in the server room in the basement, making changes and updates. Time passed oddly in the windowless, climate controlled room, lined with electronics. He hadn’t realized how late it was and by the time he exited the elevator on the 40th floor, the bullpen was empty and the only light was coming from Cat’s office. 

Her screens weren’t filled with the usual newsfeeds and constant barrage of voices. Instead, as Winn approached his own desk, he realized that the images on the screens were that of his Walking Dead video game. 

“Come on you undead bastards, come at me.” Three zombies died onscreen in rapid succession. Winn grinned to himself and collected his Red Vines from the stash in his desk.

He made his way silently to one of the chairs in front of the desk and watched in amused admiration for a few minutes. She was a natural. He couldn’t suppress a chuckle and at the sound, Cat jumped and whipped around to face him. Her face darkened and he held out the candy as a peace offering. She grabbed one length of candy and turned back to her game, hardly even acknowledging his presence.

Emboldened by his past exchanges with Cat, buoyed by his recent reconciliation with Kara and a need to explain Kara’s odd behavior the other day, Winn spoke first.

“It wasn’t her, y’know. The other day. When she was acting so weird. She can’t ever know that I told you this, but it wasn’t her.”

Cat pursed her lips and put down another half dozen walkers. “And I suppose you were an accomplice in that particular deception.”

“She was sick. We… thought you’d fire her. And, Miss Grant.... Kara loves this job. She needs it.”

Cat gave a ladylike snort and began slamming the controller buttons with unnecessary force.

In the following minutes, Winn would question both his sanity and his will to live, but the look on Kara’s face when she met her replacement and the sag in her shoulders when she was dismissed from work early that afternoon gave him a superhero’s courage. He cleared his throat and prepared for his demise. “You didn’t need to hire Siobhan.”

“And you don’t need to spend your entire day staring at her, but here we are.”

“What? I don’t… stare… Miss Grant. I just… don’t trust her, so I’m keeping an eye on her. That’s all…” He trailed off. He knew that excuse wouldn’t fly.

“Good night, Winslow.” Cat took another Red Vine from the package and returned to her game.

XX

When Max Lord had said that it was Kara herself that threw Cat from her balcony, his heart sank to his feet and he forgot to breathe.

“Miss Grant’s dead?” He could hardly get the words out.

“No, Cat’s fine, she has nine lives.” Max’s bravado incensed him and as soon as he was able, Winn raced back into the city to find Cat, shaken but strong, sipping bourbon in her office. She was standing at the open door to her balcony, just inside as though willing herself to step out.

“Miss Grant!” Winn ran across her office and swept her into a surprise hug before Cat could protest. “I’m really glad you’re not dead,” he whispered into her shoulder.

Cat patted him on the back awkwardly. “Yes, well. I’m alright. Chin up, Winslow. I need your help.” She pulled him back and gave him a squeeze on his shoulder with her free hand. She handed him the bourbon in her other. “Find your courage, dear boy. And find me a camera. I’m going live in an hour.”

XX

Cat dabbed at an errant tear with her knuckle and avoided Winn’s watchful eyes. Winn gave her a couple of minutes on her own while he packed up the camera and poured her a drink from the bar. Something told him Red Vines weren’t going to cut it tonight.

Cat accepted the drink and sipped, still refusing to look directly at him. Winn leaned against the desk next to Cat’s chair, not unlike the way Cat had done the night he’d faced his own rejection by the woman that nearly killed Cat tonight. He laid his hand over Cat’s on the desk as she took another sip. “She’s sick.”

“That seems to be something of a pattern.”

Winn squeezed her fingers. “But they’re going to fix her.”

“I hope you’re right.”

A commotion on one of the screens behind the desk drew their attention and, hand still clasped together, they watched as Supergirl battled with her own city and family until she was taken down by a horrifying looking weapon. They couldn’t see her once the area was swarmed with agents. Cat clicked off the television, polished off her drink and patted Winn’s hand. “You should go. See if she needs you.”

“Are you sure you don’t need me?”

Cat smiled.. She stood and cupped his cheek affectionately. “Go. Winslow. I’ll be fine, I promise.” It was the interrupting ring of Winn’s cellphone that made the decision for him. “Chop chop,” Cat finished.

Winn gave her a wan smile and left the office.

XX

When his head stopped splitting open and he was pretty sure his brain wasn’t going to ooze out of his ears any longer, he looked over to be sure James was okay. James gave him a little wave and smile and Winn opted for crawling into Cat’s office. He didn’t feel like he could trust his knees quite yet. 

Cat was sitting on the floor with her back propped against the front of her sofa. She was taking long, cleansing breaths and still clutching her head.

Winn sat next to her but didn’t feel compelled to say anything.

After a quiet minute, a pair of enormous shoes crossed the plush carpet. Neither of them looked up, but they heard the sound of three drinks being poured. The shoes crossed back over to the sofa and James Olsen deposited a tumbler in each of their hands before lowering himself to the floor next to Winn. No words were said. None were needed. In tandem three hands brought drinks to lips and were lowered again simultaneously. The three of them stared straight ahead, sharing the silence. After another minute, without prior warning, Cat lowered her head slowly onto Winn’s steady shoulder. His heart warmed a bit and he tipped his head and laid his own head lightly atop hers.

XX

“You’re leaving?” He didn’t mean to sound like a teenage boy, but his voice squeaked with emotion and he didn’t want to pretend like it hadn’t.

Cat sighed and sipped her drink, not leaving her spot overlooking her city. “What are you doing here, Winslow? You don’t work here anymore.”

“Don’t go.”

Cat chuckled. “You and Kara, I swear. Cardigans and melodrama all the way down.”

Winn shoved his hands into his pockets. “I know you probably don’t give as much value to our time together as I do, Miss Grant, but… that time is important to me. You’re my friend. And I’ll miss you.”

“Oh, Winn. Of course I value our friendship. But, I won’t be gone forever.” She stepped closer to him and reached out a hand to straighten his bowtie.” He could tell she was holding back tears. “I’ll need you to look after her for me.” Winn nodded and swallowed his own tears. “Don’t let her get maudlin or too angry or jaded. Keep her inspired and keep her kind.”

Winn leaned his elbows on the balustrade. “What makes you think I’m the right person for that job.”

“Because you,” Cat poked him in his bicep, “are inspired and kind. And of the people I’ve met in her life, you are the most likely candidate to stay that way through all of the things you all see every day.” Cat looked up at the stars above National City. “She has so much pain. She masks it, but it’s there. Don’t let her fall into it too deeply.”

Winn nodded. “Yeah. Yeah, okay.” On an impulse, he pulled her into a hug and for the second time that day, Cat found herself with an armful of overly sentimental millennial. “You should tell her, you know,” Winn said as he pulled away. “How much you care about her. It wouldn’t be like it was with me. She adores you.”

Cat stood on tiptoes and pressed an affectionate kiss to Winn’s stubbly cheek. “Goodbye, Winslow.”

Winn brushed his cheek with his fingertips and smiled as he turned to go. “Bye, Cat.”

XX

When James had left in his metal suit to keep fighting aliens, Cat looked around her ruined office before her eyes landed on Winn. “Is constantly being in danger of losing my life in a horrible way a typical side effect of knowing her, or are we just unlucky?”

Winn dug around in his messenger bag for a second and produced an almost full bag of Red Vines. He offered one to Cat. “Actually, I think it’s more a side effect of loving her, but… as I’m sure you’re aware… to know her is to love her.”

Cat accepted the candy and took a bite. “Indeed.” She tilted her head to the side. “So, Winslow, how long until you get a supersuit of your very own?”

Winn chuckled. “This is my supersuit, Miss Grant.”

“Well, you’re certainly a hero to me.” She sauntered to the bar. “Now, we’re taking a time out to have a drink before we head back to find the others, and you’re going to tell me all about this boyfriend of Kara’s.”

Winn rolled his eyes. “We’re gonna need a lot more booze.”

XX

Winn stopped in Noonan’s after work. The DEO was working on cleaning up the city after the battle and all seemed to be quiet on the alien front since the Daxamite exodus. CatCo Plaza was between the DEO and his apartment and if he knew Kara, she’d be burning the midnight oil working on a follow-up to the invasion story.

Bag of sticky buns in one hand and tray of coffees in the other, he tapped twice on Kara’s office door and opened it before getting permission.

“Hey, Kara, thought you might need a break from Snapper-- Woah! Nope!” Winn was met with two surprised pairs of eyes. One, Kara’s bright, piercing blue, the other Cat’s cool, keen hazel. Both faces were pink and flushed. Cat sat on top of Kara’s pristine, white desk with her back to the door and between long slender legs stood Kara, mouth frozen open and fingers hastily pulling up the golden zipper that had previously been halfway down the back of Cat’s rose-colored dress. “I’ll… just… leave you alone and never ever enter this office again… ever.”

He slammed the door shut and dropped the bag and coffees on the floor just outside. “I’m going to leave these here… in case you get… hungry later?” He winced and banged his head against the doorjamb. “Shut up, Winn,” he said to himself.

As he turned to leave he heard Cat’s amused voice through the door. “I just refilled my bourbon. Help yourself!”

“Uh, yeah. Yep. I’m gonna go… take advantage of that.” He rubbed his hands over his face and barely heard Cat call back as he was walking away.”

“Good to see you, Winslow!”


End file.
